Chop tomatoes into thirds. Put on a cookie sheet, along with garlic, onion, and shallot. Roast for about 20 minutes.
Remove veggies from the oven. Place in a large sauce pan, add diced tomatoes, basil, parsley, chicken stock, milk and half & half.
Using an immersion blender, blend mixture until it is nearly smooth. I left mine a little "pulpy" if you will because I wanted some texture, but you can blend it as much as you would like. Once blended, turn heat to about medium, add spices, stir and bring to a boil. Turn heat down to low and let simmer for 20 minutes.
While soup is simmering, prepare croutons. Layer bread slices with cheese, then cut into tiny squares. Bake for 10 minutes until cheese is melted and bread is crispy